Tetrahydrofuran → HCID 56621485, compound

HRID 1263421Notes

Reaction equation

HRID 1263421 reaction equation
[NH2:1][C@H:2]1[CH2:8][CH2:7][CH2:6][CH2:5][N:4]([CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:3]1=[O:17].[C:18](=[O:21])([O-])[O-:19].[Na+].[Na+].[CH2:24]1[CH2:28]O[CH2:26][CH2:25]1>O>[CH:24]1[C:28]2[CH:2]([CH2:3][O:19][C:18]([NH:1][C@H:2]3[CH2:8][CH2:7][CH2:6][CH2:5][N:4]([CH2:9][C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])[C:3]3=[O:17])=[O:21])[C:8]3[C:25](=[CH:26][CH:5]=[CH:6][CH:7]=3)[C:24]=2[CH:28]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 10340Sodium CarbonateHCID 10633927HCID 10633927, compound

Product 1

HCID 56621485HCID 56621485, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of tert-butyl (3S)-3-amino-2-oxoperhydroazepine-1-acetate (7 g) in THF (50 me) was added to a solution of sodium carbonate (3 g) in water (30 ml). A solution of N-(9-fluorenylmethoxycarbonyloxy)succimimide (9.7 g) in THF (100 ml) was then added dropwise over 30 minutes with stirring. The reaction mixture was stired at ambient temperature for a further 30 minutes. Water (200 ml) was added and the reaction mixture extracted with ethyl acetate (3×100 ml). The combined extracts were washed with brine (100 ml), dried (MgSO4) and evaporated. The residue was purified by MPLC on silica, eluting initially with dichloromethane and gradually increasing to 15% ethyl acetate/dichloromethane to give tert-butyl (3S)-3-(9-fluorenylmethoxycarbonylamino)-2-oxoperhydroazepine-1-acetate (10.9 g) as a clear oil; NMR (d6-DMSO): 1.45 (s, 9H), 1.5-2.15 (m, 6H), 3.1-3.25 (m, 1H), 3.6-3.75 (m, 1H), 4.0-4.5 (m, 5H), 6.25 (d, 1H), 7.25-7.45 (m, 4H), 7.6 (d, 2H), 7.75 (d, 2H); mass spectroscopy, m/e (ES+) 465.2 (MH+).

Workup

  1. extractionthe reaction mixture extracted with ethyl acetate (3×100 ml)
  2. washThe combined extracts were washed with brine (100 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by MPLC on silica
  6. washeluting initially with dichloromethane
  7. temperaturegradually increasing to 15% ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-d1886830caf24d9cbb200e555b6e1ad7
Source dataset
uspto-grants-2003_04
Patent number
US06541453B2

Reaction notes

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